The Chrysler brand is celebrating its 100th birthday in 2025 and to highlight some of the historical vehicles from the past, the company held a small media event on Detroit’s Belle Isle. In addition to an array of concept cars on display, we got to drive a handful of some of the most significant models in the brand’s history. The first vehicle that I drove and reviewed was the 1955 Chrysler C-300 and today, I am going to talk about my time with the 1958 Chrysler 300D.
The 1958 Chrysler 300D was part of the second generation of the 300 line, and like the 300C which introduced the second generation, the ‘58 300D came equipped with the 392 cubic inch Hemi V8 topped by twin four-barrel carburetors. This engine sent 380 horsepower and 435 lb-ft of torque towards the rear wheels with help from a 3-speed TorqueFlite automatic transmission, which was controlled by a push-button panel on the far left of the dashboard. There is no “park” button, so the car starts in Neutral and then you select the drive gear – either Drive, 1st, 2nd or Reverse – by pushing the appropriate button.
When I had my time to test drive the 1958 Chrysler 300D, the transmission was a little hot, so when you put it into gear, it would pull the engine speed down a ton and it would stall. A few people before me were unable to keep it running, but knowing my familiarity with classic cars, the crew monitoring the cars asked if I wanted to give it a shot. Understanding that you just needed to preload the torque convertor a bit and keep the engine speed up, I was able to get the 300D into gear and out of the parking lot on my first try.
Prior to driving the 1958 Chrysler 300D, I was told that this particular car had recently been tuned up more recently than some of the other 50s-era cars in the group, and that was evident based on how well it performed. The shifts from the TorqueFlite transmission were as firm as you want, and when you asked for power, the 392 Hemi was quick to respond. Belle Isle was quite crowded with both pedestrians and traffic, as well as police officers who were closely monitoring the 25mph speed limit, so it wasn’t like I was making high speed pulls or even had digs from a stop, but a few gentle “pulls” from stop signs and a very short stint through the mid-range made it clear that this antique muscle car packed pretty awesome power. Of course, it did all of that with the beautiful exhaust note of a Hemi V8, which has a pretty similar lope to that of the later, larger dual quad Hemi engines.
What really struck me the most about the 1958 Chrysler 300D was how vastly it differed from the 1955 Chrysler C-300 I had driven moments before the 300D. Even though there was only a three year difference between the two cars, the 300D had much sharper steering in addition to benefitting from the 3-speed transmission over the 2-speed in the ‘55. Of course, the 300D also packs quite a bit more power, so when coupled with the fact that it was more recently tuned-up, the ‘58 clearly offered a substantial improvement in performance over the legendary C-300.
There were some other aspects of the 1958 Chrysler 300C that made it unique from the 1955 C-300. First and foremost, the 1955 does not have any outside mirrors, which was fairly common when the car was new, but it is very strange by modern standards. You do not realize how often you use your mirrors until they are gone, and although I am used to not having a passenger-side mirror on my 1972 Dodge Demon 340, it has been more than a decade since I have driven a car with no exterior mirrors. Belle Isle was pretty busy when we were driving, so it was a bit nerve-racking when changing lanes in traffic without exterior mirrors. On the other hand, the 1958 300D has exterior mirrors, but they are not mounted on the A pillar. Instead, they are mounted a few feet forward, on the front fenders, so you have to make sure to adjust them before getting into the car, as there is no way to reach them from the driver’s seat. Also, the rearview mirror of the 300D is mounted on the top of the dashboard rather than on the windshield, like the C-300. I suspect that they picked this location to allow for shared parts between the hardtop and convertible models, and at first, I wondered if the lower mounting location would limit functionality, but with the overall shape of the car and the interior, that lower rearview mirror offered a great look at the road behind me.
While the 1958 Chrysler 300D does not carry the same legendary status as the 1955 C-300, it is truly a remarkable performance car from the 1950s that shows how much effort the company was putting into continuous advancements. The C-300 was a great car in 1955 and each year, Chrysler made sure to make significant improvements, which is showcased by the 1958 300D.
Click here for a look at my drive impressions of the 1955 Chrysler C-300.
Patrick Rall is a professional writer and photographer with a passion for all things automotive. Having grown up in his father’s performance shop, he spent extensive time at the oval track and drag strip – both driving and wrenching on various types of vehicles. In addition to working as a writer, Patrick previously worked as an automotive technician before moving on to a business office position with a chain of dealerships, and this broad spectrum of experience in the industry allows him to offer a unique look on the automotive world. Follow Patrick on Twitter, Facebook and on Youtube.
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